1,1'-Carbonyldiimidazole → HCID 178438835, compound

HRID 1947195Notes

Reaction equation

HRID 1947195 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([CH:23]([CH3:25])[CH3:24])=[CH:11][C:10]=1[C:26](=[N:40][NH2:41])[NH:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)=[CH:30][CH:29]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:42](N1C=CN=C1)(N1C=CN=C1)=[O:43]>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:12]([CH:23]([CH3:25])[CH3:24])=[CH:11][C:10]=1[C:26]1[N:27]([C:28]2[CH:33]=[CH:32][C:31]([N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[CH:30][CH:29]=2)[C:42]([OH:43])=[N:41][N:40]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 178439251HCID 178439251, compound

Product 1

HCID 178438835HCID 178438835, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,4-bis-benzyloxy-5-isopropyl-N-[4-(morpholin-4-yl)-phenyl]-benzene-carbohydrazonamide (F370-IM4: crude product) was suspended in tetrahydrofuran (10 mL), mixed with 1,1′-carbonyldiimidazole (1.12 g, 6.9 mmol) and the mixture was stirred at room temperature for 2 hours. The reaction mixture was partitioned between ethyl acetate (50 mL) and 5% aqueous sodium hydrogencarbonate (50 mL), and the organic layer was separated. The organic layer obtained was dried over anhydrous sodium sulfate. Sodium sulfate was removed by filtration, and the solvent was distilled off under reduced pressure, and the residue thus obtained was purified by silica gel column chromatography (ethyl acetate 100%). The obtained product was purified by suspending in ethyl acetate to obtain the title compound (F370-IM5: white crystals, 1.2 g, 45% in 3 steps).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate (50 mL) and 5% aqueous sodium hydrogencarbonate (50 mL)
  2. customthe organic layer was separated
  3. customThe organic layer obtained
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customSodium sulfate was removed by filtration
  6. distillationthe solvent was distilled off under reduced pressure
  7. customthe residue thus obtained
  8. customwas purified by silica gel column chromatography (ethyl acetate 100%)
  9. customThe obtained product was purified

Sources & evidence

ORD record
ord-923d5b1b8a5b4e3793646073fe5301bd
Source dataset
uspto-grants-2013_03
Patent number
US08399464B2

Reaction notes

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